Editing Pyrene (section)

===Reactions===
Oxidation with [[Chromate ion|chromate]] affords perinaphthenone and then naphthalene-1,4,5,8-tetracarboxylic acid. Pyrene undergoes a series of [[hydrogenation]] reactions and is susceptible to halogenation, [[Diels-Alder]] additions, and nitration, all with varying degrees of selectivity.<ref name=Ullmann/>  Bromination occurs at one of the 3-positions.<ref>{{cite journal | last1 = Gumprecht | first1 = W. H. | year = 1968 | title = 3-Bromopyrene | journal = Org. Synth. | volume = 48 | page = 30 | doi = 10.15227/orgsyn.048.0030 }}</ref>

Reduction with sodium affords the radical anion. From this anion, a variety of pi-arene complexes can be prepared.<ref>{{cite journal |doi=10.1107/S2053229614015290|title=Bis(pyrene)metal complexes of vanadium, niobium and titanium: Isolable homoleptic pyrene complexes of transition metals|year=2014|last1=Kucera|first1=Benjamin E.|last2=Jilek|first2=Robert E.|last3=Brennessel|first3=William W.|last4=Ellis|first4=John E.|journal=Acta Crystallographica Section C: Structural Chemistry|volume=70|issue=8|pages=749–753|pmid=25093352}}</ref>